2-(4-Isobutyl-phen-yl)-N'-[(3Z)-2-oxoindolin-3-yl-idene]propano-hydrazide.

In the title compound, C(21)H(23)N(3)O(2), the indolin-2-one group is essentially planar, with a maximum deviation of 0.016 (2) Å for the N atom, and makes a dihedral angle of 84.38 (14)° with the benzene ring. The =N-N(H)-C(=O)-C- torsion angle is 0.9 (3)°. In the crystal, mol-ecules are linked into a three-dimensional network via N-H⋯O and C-H⋯O hydrogen bonds. In addition, a C-H⋯π inter-action was observed.

Related literature

For the pharmaceutical applications of hydrazones, see: Bedia et al. (2006 ▶); Rollas et al. (2002 ▶). For the pharmaceutical applications of ibuprofen, see: Palaska et al. (2002 ▶). For the synthesis of hydrazones, see: Rollas & Küçükgüzel (2007 ▶). For some of our studies on the synthesis of biologically active compounds, see: Mohamed et al. (2012a ▶,b ▶); Soliman et al. (2012 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C21H23N3O2

M = 349.42

Monoclinic,

a = 30.366 (14) Å

b = 7.383 (3) Å

c = 21.904 (10) Å

β = 130.311 (8)°

V = 3745 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 150 K

0.35 × 0.21 × 0.10 mm

Data collection

Bruker APEX 2000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.972, T max = 0.992

15933 measured reflections

4494 independent reflections

2050 reflections with I > 2σ(I)

R int = 0.096

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.182

S = 0.89

4494 reflections

223 parameters

H-atom parameters constrained

Δρmax = 0.60 e Å−3

Δρmin = −0.39 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681201269X/hg5199sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201269X/hg5199Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681201269X/hg5199Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H23N3O2	F(000) = 1488
Mr = 349.42	Dx = 1.240 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 654 reflections
a = 30.366 (14) Å	θ = 2.9–23.4°
b = 7.383 (3) Å	µ = 0.08 mm−1
c = 21.904 (10) Å	T = 150 K
β = 130.311 (8)°	Plate, yellow
V = 3745 (3) Å3	0.35 × 0.21 × 0.10 mm
Z = 8

Bruker APEX 2000 CCD area-detector diffractometer	4494 independent reflections
Radiation source: fine-focus sealed tube	2050 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.096
phi and ω scans	θmax = 28.7°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −40→39
Tmin = 0.972, Tmax = 0.992	k = −9→9
15933 measured reflections	l = −29→28

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.182	H-atom parameters constrained
S = 0.89	w = 1/[σ2(Fo2) + (0.0771P)2] where P = (Fo2 + 2Fc2)/3
4494 reflections	(Δ/σ)max < 0.001
223 parameters	Δρmax = 0.60 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O1	0.27378 (8)	0.1979 (3)	0.28135 (11)	0.0610 (8)
O2	0.30262 (7)	−0.3536 (2)	0.51498 (11)	0.0551 (7)
N1	0.21763 (9)	0.3981 (3)	0.28414 (12)	0.0513 (8)
N2	0.26682 (8)	−0.0134 (3)	0.38256 (12)	0.0441 (7)
N3	0.26590 (8)	−0.1154 (3)	0.43261 (12)	0.0438 (7)
C1	0.19248 (10)	0.4090 (3)	0.31931 (14)	0.0449 (9)
C2	0.16039 (11)	0.5488 (4)	0.31409 (15)	0.0536 (9)
C3	0.13834 (11)	0.5291 (4)	0.35241 (16)	0.0552 (10)
C4	0.14805 (11)	0.3748 (4)	0.39497 (16)	0.0518 (10)
C5	0.18120 (10)	0.2344 (3)	0.40110 (14)	0.0462 (8)
C6	0.20363 (9)	0.2513 (3)	0.36274 (13)	0.0406 (8)
C7	0.23936 (10)	0.1382 (3)	0.35482 (14)	0.0426 (8)
C8	0.24645 (11)	0.2419 (4)	0.30246 (15)	0.0480 (9)
C9	0.30217 (10)	−0.2603 (3)	0.46825 (15)	0.0445 (8)
C10	0.34176 (10)	−0.2953 (3)	0.45024 (15)	0.0469 (9)
C11	0.36252 (12)	−0.4915 (4)	0.47037 (18)	0.0631 (11)
C12	0.39149 (10)	−0.1604 (3)	0.49514 (16)	0.0445 (9)
C13	0.43620 (11)	−0.1733 (4)	0.57647 (16)	0.0511 (10)
C14	0.48254 (11)	−0.0548 (4)	0.61611 (17)	0.0571 (10)
C15	0.48610 (12)	0.0796 (4)	0.57581 (19)	0.0556 (10)
C16	0.44102 (12)	0.0942 (4)	0.49473 (19)	0.0583 (11)
C17	0.39438 (12)	−0.0220 (4)	0.45516 (17)	0.0533 (10)
C18	0.53791 (12)	0.2047 (4)	0.6173 (2)	0.0705 (13)
C19	0.52905 (13)	0.3956 (4)	0.63358 (19)	0.0679 (7)
C20	0.58104 (12)	0.5126 (4)	0.66581 (18)	0.0679 (7)
C21	0.51718 (12)	0.3939 (4)	0.68999 (18)	0.0679 (7)
H1	0.21500	0.48110	0.25440	0.0620*
H2	0.15370	0.65350	0.28560	0.0640*
H3	0.11640	0.62220	0.34950	0.0660*
H3A	0.24300	−0.08990	0.44180	0.0530*
H4	0.13230	0.36450	0.41980	0.0620*
H5	0.18820	0.13090	0.43040	0.0550*
H10	0.31960	−0.27740	0.39270	0.0560*
H11A	0.38740	−0.51360	0.45840	0.0950*
H11B	0.32980	−0.57130	0.43910	0.0950*
H11C	0.38340	−0.51290	0.52630	0.0950*
H13	0.43530	−0.26330	0.60530	0.0610*
H14	0.51190	−0.06620	0.67120	0.0690*
H16	0.44200	0.18430	0.46600	0.0700*
H17	0.36430	−0.00710	0.40050	0.0640*
H18A	0.54900	0.21270	0.58470	0.0850*
H18B	0.56990	0.15020	0.66790	0.0850*
H19	0.49540	0.44780	0.58270	0.0810*
H20A	0.58750	0.51340	0.62830	0.1020*
H20B	0.61440	0.46460	0.71610	0.1020*
H20C	0.57410	0.63400	0.67350	0.1020*
H21A	0.48390	0.32030	0.66820	0.1020*
H21B	0.51010	0.51530	0.69750	0.1020*
H21C	0.54990	0.34500	0.74060	0.1020*

	U11	U22	U33	U12	U13	U23
O1	0.0792 (14)	0.0562 (13)	0.0671 (13)	0.0042 (10)	0.0561 (12)	−0.0018 (10)
O2	0.0503 (11)	0.0447 (11)	0.0692 (13)	0.0100 (8)	0.0381 (10)	0.0125 (10)
N1	0.0603 (14)	0.0449 (14)	0.0494 (13)	0.0086 (11)	0.0358 (12)	0.0091 (11)
N2	0.0440 (12)	0.0377 (13)	0.0491 (12)	0.0025 (10)	0.0294 (11)	−0.0028 (10)
N3	0.0415 (12)	0.0376 (12)	0.0540 (13)	0.0078 (9)	0.0316 (11)	0.0026 (10)
C1	0.0454 (15)	0.0418 (16)	0.0387 (14)	0.0060 (12)	0.0232 (13)	−0.0001 (12)
C2	0.0568 (16)	0.0387 (16)	0.0482 (16)	0.0117 (13)	0.0263 (14)	0.0041 (13)
C3	0.0562 (17)	0.0466 (17)	0.0532 (16)	0.0140 (13)	0.0311 (15)	−0.0016 (14)
C4	0.0547 (16)	0.0478 (17)	0.0545 (17)	0.0088 (13)	0.0360 (14)	−0.0005 (14)
C5	0.0448 (14)	0.0406 (15)	0.0456 (14)	0.0058 (12)	0.0258 (13)	−0.0013 (12)
C6	0.0394 (13)	0.0342 (14)	0.0396 (13)	0.0044 (11)	0.0217 (12)	−0.0016 (11)
C7	0.0417 (14)	0.0358 (14)	0.0417 (14)	0.0020 (11)	0.0231 (12)	−0.0029 (11)
C8	0.0532 (16)	0.0434 (16)	0.0435 (14)	0.0009 (13)	0.0295 (14)	−0.0058 (13)
C9	0.0387 (14)	0.0336 (14)	0.0517 (15)	0.0017 (11)	0.0250 (13)	−0.0039 (13)
C10	0.0461 (15)	0.0420 (16)	0.0503 (15)	0.0079 (12)	0.0302 (13)	−0.0044 (12)
C11	0.0606 (18)	0.0435 (18)	0.081 (2)	0.0089 (14)	0.0439 (17)	−0.0083 (15)
C12	0.0421 (14)	0.0431 (16)	0.0563 (16)	0.0105 (12)	0.0354 (14)	−0.0026 (13)
C13	0.0471 (15)	0.0458 (17)	0.0614 (18)	0.0061 (13)	0.0356 (15)	0.0005 (14)
C14	0.0444 (16)	0.0588 (19)	0.0588 (17)	0.0081 (14)	0.0292 (15)	−0.0030 (15)
C15	0.0484 (16)	0.0472 (18)	0.079 (2)	0.0078 (13)	0.0447 (17)	−0.0033 (15)
C16	0.0610 (18)	0.0468 (18)	0.081 (2)	0.0095 (14)	0.0522 (18)	0.0074 (16)
C17	0.0545 (17)	0.0521 (18)	0.0603 (17)	0.0114 (14)	0.0403 (15)	0.0012 (15)
C18	0.0526 (17)	0.058 (2)	0.104 (3)	0.0077 (15)	0.0520 (19)	−0.0014 (18)
C19	0.0653 (11)	0.0599 (12)	0.0753 (12)	0.0005 (9)	0.0441 (10)	0.0013 (10)
C20	0.0653 (11)	0.0599 (12)	0.0753 (12)	0.0005 (9)	0.0441 (10)	0.0013 (10)
C21	0.0653 (11)	0.0599 (12)	0.0753 (12)	0.0005 (9)	0.0441 (10)	0.0013 (10)

O1—C8	1.227 (5)	C16—C17	1.380 (5)
O2—C9	1.227 (4)	C18—C19	1.520 (5)
N1—C1	1.394 (5)	C19—C21	1.494 (6)
N1—C8	1.343 (4)	C19—C20	1.515 (6)
N2—N3	1.345 (3)	C2—H2	0.9300
N2—C7	1.289 (3)	C3—H3	0.9300
N3—C9	1.362 (4)	C4—H4	0.9300
N1—H1	0.8600	C5—H5	0.9300
N3—H3A	0.8600	C10—H10	0.9800
C1—C6	1.399 (3)	C11—H11A	0.9600
C1—C2	1.373 (5)	C11—H11B	0.9600
C2—C3	1.379 (5)	C11—H11C	0.9600
C3—C4	1.378 (4)	C13—H13	0.9300
C4—C5	1.390 (5)	C14—H14	0.9300
C5—C6	1.388 (5)	C16—H16	0.9300
C6—C7	1.466 (4)	C17—H17	0.9300
C7—C8	1.506 (4)	C18—H18A	0.9700
C9—C10	1.510 (5)	C18—H18B	0.9700
C10—C12	1.523 (4)	C19—H19	0.9800
C10—C11	1.527 (4)	C20—H20A	0.9600
C12—C13	1.377 (4)	C20—H20B	0.9600
C12—C17	1.385 (4)	C20—H20C	0.9600
C13—C14	1.385 (5)	C21—H21A	0.9600
C14—C15	1.378 (5)	C21—H21B	0.9600
C15—C18	1.518 (5)	C21—H21C	0.9600
C15—C16	1.376 (5)
C1—N1—C8	111.6 (2)	C3—C2—H2	121.00
N3—N2—C7	121.5 (3)	C2—C3—H3	119.00
N2—N3—C9	118.1 (3)	C4—C3—H3	119.00
C8—N1—H1	124.00	C3—C4—H4	120.00
C1—N1—H1	124.00	C5—C4—H4	120.00
C9—N3—H3A	121.00	C4—C5—H5	121.00
N2—N3—H3A	121.00	C6—C5—H5	121.00
N1—C1—C2	127.6 (2)	C9—C10—H10	108.00
C2—C1—C6	121.9 (3)	C11—C10—H10	108.00
N1—C1—C6	110.5 (2)	C12—C10—H10	108.00
C1—C2—C3	117.9 (3)	C10—C11—H11A	109.00
C2—C3—C4	121.6 (3)	C10—C11—H11B	109.00
C3—C4—C5	120.5 (3)	C10—C11—H11C	109.00
C4—C5—C6	118.9 (2)	H11A—C11—H11B	110.00
C1—C6—C7	105.4 (3)	H11A—C11—H11C	109.00
C5—C6—C7	135.3 (2)	H11B—C11—H11C	109.00
C1—C6—C5	119.3 (3)	C12—C13—H13	119.00
N2—C7—C8	115.7 (3)	C14—C13—H13	119.00
C6—C7—C8	106.4 (2)	C13—C14—H14	119.00
N2—C7—C6	137.9 (3)	C15—C14—H14	119.00
O1—C8—N1	125.7 (3)	C15—C16—H16	119.00
O1—C8—C7	128.1 (3)	C17—C16—H16	119.00
N1—C8—C7	106.1 (3)	C12—C17—H17	119.00
O2—C9—N3	119.2 (3)	C16—C17—H17	119.00
N3—C9—C10	118.0 (2)	C15—C18—H18A	108.00
O2—C9—C10	122.7 (2)	C15—C18—H18B	108.00
C9—C10—C11	109.7 (3)	C19—C18—H18A	108.00
C9—C10—C12	110.1 (2)	C19—C18—H18B	108.00
C11—C10—C12	112.5 (3)	H18A—C18—H18B	107.00
C13—C12—C17	117.2 (3)	C18—C19—H19	108.00
C10—C12—C13	121.8 (3)	C20—C19—H19	108.00
C10—C12—C17	121.1 (2)	C21—C19—H19	108.00
C12—C13—C14	121.3 (3)	C19—C20—H20A	109.00
C13—C14—C15	121.5 (3)	C19—C20—H20B	109.00
C14—C15—C16	117.3 (3)	C19—C20—H20C	109.00
C14—C15—C18	122.4 (3)	H20A—C20—H20B	110.00
C16—C15—C18	120.4 (3)	H20A—C20—H20C	110.00
C15—C16—C17	121.4 (3)	H20B—C20—H20C	109.00
C12—C17—C16	121.4 (3)	C19—C21—H21A	109.00
C15—C18—C19	115.6 (4)	C19—C21—H21B	110.00
C18—C19—C21	111.1 (3)	C19—C21—H21C	110.00
C20—C19—C21	110.8 (3)	H21A—C21—H21B	109.00
C18—C19—C20	110.4 (4)	H21A—C21—H21C	109.00
C1—C2—H2	121.00	H21B—C21—H21C	109.00
C1—N1—C8—C7	0.3 (3)	C6—C7—C8—O1	179.0 (3)
C8—N1—C1—C2	179.5 (3)	C6—C7—C8—N1	0.5 (3)
C8—N1—C1—C6	−1.1 (3)	N2—C7—C8—O1	2.1 (4)
C1—N1—C8—O1	−178.2 (3)	O2—C9—C10—C11	21.8 (3)
N3—N2—C7—C8	177.3 (2)	O2—C9—C10—C12	−102.5 (3)
C7—N2—N3—C9	−171.0 (2)	N3—C9—C10—C11	−160.3 (2)
N3—N2—C7—C6	1.7 (5)	N3—C9—C10—C12	75.4 (3)
N2—N3—C9—C10	0.9 (3)	C9—C10—C12—C13	73.9 (4)
N2—N3—C9—O2	179.0 (2)	C9—C10—C12—C17	−108.0 (3)
N1—C1—C6—C7	1.4 (3)	C11—C10—C12—C13	−48.8 (4)
C2—C1—C6—C5	0.7 (4)	C11—C10—C12—C17	129.4 (3)
C2—C1—C6—C7	−179.2 (2)	C10—C12—C13—C14	177.0 (3)
N1—C1—C6—C5	−178.8 (2)	C17—C12—C13—C14	−1.2 (5)
C6—C1—C2—C3	−0.9 (4)	C10—C12—C17—C16	−176.1 (3)
N1—C1—C2—C3	178.5 (3)	C13—C12—C17—C16	2.1 (5)
C1—C2—C3—C4	0.2 (4)	C12—C13—C14—C15	−0.6 (6)
C2—C3—C4—C5	0.7 (5)	C13—C14—C15—C16	1.5 (6)
C3—C4—C5—C6	−0.9 (4)	C13—C14—C15—C18	−176.8 (4)
C4—C5—C6—C7	−180.0 (3)	C14—C15—C16—C17	−0.6 (6)
C4—C5—C6—C1	0.2 (4)	C18—C15—C16—C17	177.7 (4)
C1—C6—C7—C8	−1.2 (3)	C14—C15—C18—C19	−104.2 (4)
C5—C6—C7—C8	179.1 (3)	C16—C15—C18—C19	77.6 (5)
C5—C6—C7—N2	−5.1 (6)	C15—C16—C17—C12	−1.2 (6)
C1—C6—C7—N2	174.7 (3)	C15—C18—C19—C20	−173.2 (3)
N2—C7—C8—N1	−176.4 (2)	C15—C18—C19—C21	63.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	1.91	2.740 (4)	163
N3—H3A···O2ii	0.86	2.16	2.965 (4)	155
C5—H5···O2ii	0.93	2.30	3.218 (3)	172
C11—H11B···Cg1iii	0.96	2.77	3.703 (4)	164

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C1/C6–C8 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	1.91	2.740 (4)	163
N3—H3A⋯O2ii	0.86	2.16	2.965 (4)	155
C5—H5⋯O2ii	0.93	2.30	3.218 (3)	172
C11—H11B⋯Cg1iii	0.96	2.77	3.703 (4)	164

Symmetry codes: (i) ; (ii) ; (iii) .